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Synthesis 2012(1): 87-92
DOI: 10.1055/s-0031-1289608
DOI: 10.1055/s-0031-1289608
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCopper(II) Triflate Promoted One-Pot Synthesis of Coumarin-, Quinolone-, and Naphthalene-Annulated 2-Aminothiazoles under Ligand-Free Conditions
Further Information
Received
12 September 2011
Publication Date:
15 November 2011 (online)
Publication History
Publication Date:
15 November 2011 (online)

Abstract
An efficient synthesis of new 2-aminothiazole-annulated compounds is described via copper(II) triflate promoted sequential condensation, arylation, and heterocyclization reactions in one step. The reaction is compatible with a variety of substrates providing efficient access to many biologically important skeletons in good yields.
Key words
copper triflate - multicomponent reaction - naphthothiazole - domino synthesis - carbon disulfide
- 1a
Vicini P.Geronikaki A.Anastasia K.Incerti M.Zani F. Bioorg. Med. Chem. 2006, 14: 3859MissingFormLabel - 1b
Caprathe BW.Jaen JC.Wise LD.Heffner TG.Pugsley TA.Meltzer LT.Parvez M. J. Med. Chem. 1991, 34: 2736MissingFormLabel - 2a
Paget CJ.Kisner K.Stone RL.DeLong DC.
J. Med. Chem. 1969, 12: 1016MissingFormLabel - 2b
Lours P. Def. Veg. 1970, 24: 91MissingFormLabel - 2c
Xin Z.Yang-fang Z.Jia W.Wei J.Liang H.Ping G. Chem. Res. Chin. Uni. 2006, 22: 459MissingFormLabel - 3a
Siddiqui N.Arshad MF.Ahsan W.Alam MS. Int. J. Pharm. Sci. Drug Res. 2009, 1: 136MissingFormLabel - 3b
Gupta A.Rawat S. J. Curr. Pharm. Res. 2010, 3: 13MissingFormLabel - 4a
Kalkhambkar RG.Kulkarni GM.Shivkumar H.Rao NR. Eur. J. Med. Chem. 2007, 42: 1272MissingFormLabel - 4b
O’Kennedy R.Thornes RD. Coumarins: Biology, Applications and Mode of Action Wiley; Chichester: 1997.MissingFormLabel - 5
El-Shishtawy RM.Asiri AM.Basaif SA.Sobahi TR. Spectrochim. Acta, Part A 2010, 75: 1605MissingFormLabel - 6
Yang Z.Li Q.Qian X. Bioorg. Med. Chem. 2005, 13: 3149MissingFormLabel - 7
Azam F.Alkskas IA.Khokra SL.Prakash O. Eur. J. Med. Chem. 2009, 44: 203MissingFormLabel - 8
Amin KM.Rahman DEA.Al-Eryani YA. Bioorg. Med. Chem. 2008, 16: 5377MissingFormLabel - 9a
Hugerschoff H. Chem. Ber. 1901, 34: 3121MissingFormLabel - 9b
Alaimo RJ. J. Heterocycl. Chem. 1971, 8: 309MissingFormLabel - 9c
Jeng L.Kasina S. J. Heterocycl. Chem. 1981, 18: 759MissingFormLabel - 10a
Dogruer DS.Unlu S.Sahin MF.Simageahin EY. Farmaco 1998, 53: 80MissingFormLabel - 10b
Naim SS.Singh SK.Sharma S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1991, 30: 494MissingFormLabel - 10c
Francisco L.Mariano M.Dolores V.Enric B.Lluís J. Tetrahedron 2004, 60: 285MissingFormLabel - 11a
Ding Q.He X.Wu J. J. Comb. Chem. 2009, 11: 587MissingFormLabel - 11b
Shen G.Lv X.Bao W. Eur. J. Org. Chem. 2009, 5897MissingFormLabel - 11c
Joyce LL.Evindar G.Batey RA. Chem. Commun. 2004, 446MissingFormLabel - 11d
Sahoo SK.Jamir L.Guin S.Patel BK. Adv. Synth. Catal. 2010, 352: 2538MissingFormLabel - 11e
Saha P.Ramana T.Purkait N.Ali MA.Paul R.Punniyamurthy T. J. Org. Chem. 2009, 74: 8719MissingFormLabel - 12a
Ding Q.Cao B.Liu X.Zong Z.Peng Y.-Y. Green Chem. 2010, 12: 1607MissingFormLabel - 12b
Wang J.Peng F.Jiang J.Lu Z.Wang L.Bai J.Pan Y. Tetrahedron Lett. 2008, 49: 467MissingFormLabel - 12c
Inamoto K.Hasegawa C.Kawasaki J.Hiroya K.Doi T. Adv. Synth. Catal. 2010, 352: 2643MissingFormLabel - 12d
Sun Y.-L.Zhang Y.Cui X.-H.Wang W. Adv. Synth. Catal. 2011, 353: 1174MissingFormLabel - 13a
Monguchi D.Fujiwara T.Furukawa H.Mori A. Org. Lett. 2009, 11: 1607MissingFormLabel - 13b
Wang Q.Schreiber SL. Org. Lett. 2009, 11: 5178MissingFormLabel - 14a
Estévez V.Villacampa M.Menéndez JC. Chem. Soc. Rev. 2010, 39: 4402MissingFormLabel - 14b
Jiang B.Rajale T.Wever W.Tu S.-J.Li G. Chem. Asian J. 2010, 5: 2318MissingFormLabel - 14c
Touré BB.Hall DG. Chem. Rev. 2009, 109: 4439MissingFormLabel - 14d
Sunderhaus JD.Martin SF. Chem. Eur. J. 2009, 15: 1300MissingFormLabel - 14e
Palasz A. Synthesis 2010, 4021MissingFormLabel - 14f
Sun J.Wu Q.Xia E.-Y.Yan C.-G. Synthesis 2010, 3987MissingFormLabel - 14g
Altieri E.Cordaro M.Grassi G.Risitano F.Scala A. Synlett 2010, 2106MissingFormLabel - 15a
Majumdar KC.Ganai S.Nandi RK. New J. Chem. 2011, 35: 1355MissingFormLabel - 15b
Majumdar KC.De N.Roy B. Synthesis 2010, 4207MissingFormLabel - 15c
Majumdar KC.Taher A.Nandi RK. Synlett 2010, 1389MissingFormLabel - 15d
Majumdar KC.Chakravorty S.Ghosh T.Sridhar B. Synlett 2010, 3127MissingFormLabel - 15e
Majumdar KC.Taher A.Ponra S. Synlett 2010, 735MissingFormLabel - 16
Ma D.Lu X.Shi L.Zhang H.Jiang Y.Liu X. Angew. Chem. Int. Ed. 2011, 50: 1118MissingFormLabel - 17
Critchfield FE.Johnson JB. Anal. Chem. 1956, 28: 430MissingFormLabel - 18
Monge A.Pena MdC.Palop JA.Caldero JM.Roca J.Garcia E.Romero G.del Rio J.Lasheras B.
J. Med. Chem. 1994, 37: 1320MissingFormLabel